Triethylamine → tert-Butyl 1-benzyl-7-(propylsulfonamidomethyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

HRID 82865Notes

Reaction equation

HRID 82865 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:35]([S:38](Cl)(=[O:40])=[O:39])[CH2:36][CH3:37]>ClCCl>[CH2:13]([CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([CH2:2][NH:1][S:38]([CH2:35][CH2:36][CH3:37])(=[O:40])=[O:39])[CH:12]=2)[CH2:7][CH2:8][CH:9]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 57471193Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Product 1

HCID 86685684tert-Butyl 1-benzyl-7-(propylsulfonamidomethyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamateYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (0.600 g, 1.637 mmol) was suspended in dichloromethane (5 mL) and triethylamine (0.228 mL, 1.637 mmol) and cooled to 0° C. 1-Propanesulfonyl chloride (0.184 mL, 1.64 mmol) was added. The solid immediately dissolved. The mixture was stirred 35 minutes, and then it was diluted with dichloromethane and washed with brine (1×50 mL). The organic phase was collected, dried on MgSO4 and the volatiles were evaporated under reduced pressure, yielding the product as a pale yellow solid (628.3 mg, 1.33 mmol, 81%).

Workup

  1. dissolutionThe solid immediately dissolved
  2. washwashed with brine (1×50 mL)
  3. customThe organic phase was collected
  4. customdried on MgSO4
  5. customthe volatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-9606b7a3272f4cd9ae3ecceadf9ef301
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

Loading…